18323-44-9

Basic information

• Product Name: Clindamycin
• Synonyms: Clindamycin (base and/or unspecified salts);(2S,4R)-N-[(1S,2S)-2-Chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide;CLDM;Methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S)-1-methyl-4β-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside;Methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside;U-21251;Clindamycin Base;7-Chloro-7-deoxylincoMycin, 7-ChlorolincoMycin
• CAS NO: 18323-44-9
• Molecular Formula: C₁₈H₃₃ClN₂O₅S
• Molecular Weight: 424.98
• EINECS: 242-209-1
• Product Categories: Inhibitors
• Mol File: 18323-44-9.mol

Chemical Properties

• Boiling Point: 134°C (rough estimate)
• Flash Point: 333.649 °C
• Appearance: /
• Density: 1.1184 (rough estimate)
• Vapor Pressure: 2.07E-18mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• PKA: 7.6(at 25℃)
• CAS DataBase Reference: Clindamycin(CAS DataBase Reference)
• NIST Chemistry Reference: Clindamycin(18323-44-9)
• EPA Substance Registry System: Clindamycin(18323-44-9)

Safety Data

• Hazardous Substances Data: 18323-44-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Clindamycin is used as an antibiotic agent for treating various bacterial infections due to its broad-spectrum activity against aerobic gram-positive cocci, gram-positive and gram-negative anaerobic bacteria, and protozoal organisms like Toxoplasma and Plasmodium species.
Used in Clinical Applications:
Clindamycin is used as a therapeutic agent for its better absorption from the gastrointestinal tract and its effectiveness against a wide range of bacteria and protozoans, making it a preferred choice over its parent compound, lincomycin.
Brand Name:
Clindamycin is commercially available under the brand name Cleocin, produced by Pharmacia & Upjohn.

Originator

Dalacin-C,Diethelm,Switz.,1968

Indications

Clindamycin (Cleocin), 300 to 450 mg/day, is an extremely effective agent for acne.

Therapeutic Function

Antibacterial

Biological Activity

Clindamycin is a lincosamide antibiotic. It is active against Gram-positive bacteria, including various strains of S. pneumoniae, S. viridans, S. aureus, and S. epidermidis (MICs = 0.002-0.1, 0.005-0.2, 0.04-1.6, and 0.1-0.2 μg/ml, respectively). Clindamycin is also active against chloroquine-resistant and -sensitive strains of P. falciparum (IC50s = 3.12 and 8.81 nM, respectively). It inhibits bacterial protein synthesis by interacting with the 50S ribosome. Clindamycin increases survival in a mouse model of a secondary S. pneumoniae infection when administered at a dose of 15 mg/kg twice daily for seven days. Formulations containing clindamycin have been used in the treatment of bacterial infections.

Contact allergens

This lincosanide antibiotic is used in topical form for acne, or systemically has been responsible for exanthematous rashes and acute generalized exanthematous pustulosis.

Mechanism of action

Clindamycin inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit. The use of clindamycin with macrolides is not recommended since both of them compete for binding sites to the 50S subunit.

Clinical Use

Clindamycin is effective in the treatment of most infections secondary to anaerobes and gram-positive cocci. It can be used for anaerobic pulmonary, intra-abdominal, gynecologic, pelvic, diabetic foot, and decubitus ulcer infections. Another appropriate agent should be added since the majority of these infections are polymicrobial. It can also be used as an alternative agent for patients with severe penicillin allergy. It is also used to treat Clostridium perfringens infection. Oral preparations of clindamycin and vaginal cream are alternatives to metronidazole for the treatment of bacterial vaginosis. Topical solution is used for treatment of acne vulgaris and rosacea. Clindamycin is extensively metabolized by the liver and the half-life is prolonged in patients with cirrhosis and hepatitis. Dose reductions are recommended in patients with acute liver disease.

Side effects

The most commonly observed adverse effect is diarrhea. The reported incidence of C. difficile colitis in patients treated with clindamycin varies from 0.1 to 10%. The syndrome may be fatal. If the patient develops C. difficile colitis, clindamycin should be discontinued and the patient should be treated for C. difficile . Other side effects include rash, nausea, vomiting, diarrhea, flatulence, abdominal distension, anorexia, and transient elevation of liver enzymes. Other less common events, such as fever, neutropenia, thrombocytopenia, and eosinophilia have been reported.

Synthesis

Clindamycin, methyl-[7-chloro-6,7,8-trideoxy-6-trans-(1-methyl-4-propylL-2-pyrrollidin-carboxamido)-1-thio-L-threo-α-D-galacto-octapyranoside] (32.5.2), which is a 7(S)-chloro-7-deoxy derivative of lincomycin, is synthesized by replacing the hydroxyl group of lincomycin (32.5.1) at C7 by treating it with triphenyl phophine in acetonitrile (Raydon reagent), in which a configuration transformation takes place in the given carbo hydrate.

Veterinary Drugs and Treatments

Topical clindamycin is an optional topical treatment for feline acne. Clindamycin inhibits bacterial protein synthesis by binding to the 50S ribosome; primary activity is against anaerobic and grampositive aerobic bacteria. For more information on the pharmacology of clindamycin, refer to the monograph for systemic use found in the main section.

Drug interactions

Potentially hazardous interactions with other drugs Ciclosporin: may cause reduced ciclosporin levels. Erythromycin: antagonism demonstrated in vitro; manufacturers recommend that the two drugs should not be administered concurrently. Muscle relaxants: enhanced neuromuscular blockade.

Metabolism

Clindamycin undergoes metabolism, presumably in the liver, to the active N-demethyl and sulfoxide metabolites, and also to some inactive metabolites. About 10% of a dose is excreted in the urine as active drug or metabolites and about 4% in the faeces; the remainder is excreted as inactive metabolites. Excretion is slow, and takes place over several days

InChI:InChI=1/C18H33ClN2O5S.ClH/c1-5-6-10-7-11(21(3)8-10)17(25)20-12(9(2)19)16-14(23)13(22)15(24)18(26-16)27-4;/h9-16,18,22-24H,5-8H2,1-4H3,(H,20,25);1H/t9-,10+,11-,12+,13-,14+,15+,16?,18+;/m0./s1

Upstream product

• 859-18-7 lincomycin hydrochloride 

Downstream Products

• 147650-54-2 C₂₁H₃₇ClN₂O₅S 
• 21462-39-5 clindamycin hydrochloride 

Relevant articles and documents

Preparation method for clindamycin hydrochloride

The invention specifically relates to a preparation method for clindamycin hydrochloride, belonging to the field of pharmaceutical chemistry. The preparation method comprises the following steps: (1) subjecting lincomycin hydrochloride and a Vilsmeier reagent to a chlorination reaction to obtain a chlorinated solution, wherein heating is gradually carried out in the process of the reaction; (2) cooling the chlorinated solution to 2 to 6 DEG C at a cooling rate of 14 to 20 DEG C/h, then carrying out a hydrolysis reaction in an aqueous solution of sodium hydroxide and then successively carrying out extraction, washing and concentration so as to obtain clindamycin free alkali; (3) subjecting the clindamycin free alkali and a saturated ethanol solution of hydrogen chloride to a salt formation reaction and carrying out crystallization, cooling, low-temperature crystallization and centrifugal washing so as to obtain a clindamycin hydrochloride alcohol adduct; and (4) subjecting the clindamycin hydrochloride alcohol adduct to dealcoholysis, crystallization, pumping filtration and drying so as to obtain clindamycin hydrochloride. Through optimization of the preparation method, yield is increased; impurity content is substantially reduced; and high-purity clindamycin hydrochloride is obtained.

A clindamycin phosphate ester synthesis method

The invention belongs to the technical field of chemical synthesis and specifically relates to a synthetic method of clindamycin phosphate. The method comprises the following steps of synthesis of clindamycin free alkali, ketonization reaction, phosphorylation reaction and aftertreatment. According to the invention, the weight yield of the clindamycin phosphate can reach over 80% by changing a charging sequence, steps and a catalyst.

Composition and method for rectal delivery of a lincosamide antibiotic drug

A suppository composition and method for rectal administration of a lincosamide antibacterial drug, such as clindamycin, lincomycin, or pirlimycin, is disclosed. The composition is a rectal suppository containing an antimicrobially effective amount of the lincosamide in particulate form dispersed in a Hard Fat suppository base, preferably a Hard Fat NF suppository base. The most preferred suppository compositions of the present invention have long term storage stability, while maintaining effectiveness against bacterial infections.

Method for treating inflammation

A method of treating inflammation comprising topical administration to mammals suffering from an inflammatory condition not associated with amicrobial component, employing selected antibiotics as the anti-inflammatory agent.